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Bobby Paoloni has a diverse work experience in the sports and service industry. Bobby started their career as a General Intern with the Lake Erie Crushers in 2016, where they gained knowledge in promotions and stadium operations. In 2017, they worked as a Student Consultant for the San Diego Padres, focusing on attracting millennial fans. Bobby then served as an Intern at TeamWork Online, handling social media and interviewing new hires for the newsletter. In 2018, they became the Music Coordinator for the Lake Erie Crushers. Bobby joined the YMCA of Greater Cleveland in 2020 as a Member Service Representative, ensuring member satisfaction and generating new memberships. Bobby also worked for the Cleveland Cavaliers as a Sales and Services Operations Crew member. Currently, they are employed at the Cleveland Guardians as a Groups Service Representative.

Bobby Paoloni attended Ohio University from 2014 to 2018. During this time, they pursued a Sports Management Major. No information regarding the completion of a degree is available.